Vaid Himani, Sharma Akashdeep, Jamwal Paru, Sharma Pryanka, Gurubrahamam Ramani
Department of Chemistry, Indian Institute of Technology Jammu, NH-44, PO Nagrota, Jagti, Jammu and Kashmir 181221, India.
Org Lett. 2024 Mar 15;26(10):2135-2140. doi: 10.1021/acs.orglett.4c00545. Epub 2024 Mar 1.
The first Doyle-Kirmse reaction on alkynyl diazoacetates using allyl/propargyl sulfides is reported. The development provides diversified 1,5-enyne and 1,4-allenyne thioaryl carboxylates in good yields under ligand-/additive-free AuCl and Rh(OAc) catalysis, respectively (48 examples, up to 96% yield). The study demonstrated the dual role of allyl sulfide as a ligand and substrate. Also, we have exemplified various synthetic modifications of the products to showcase the utility of different functional groups.
